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Conjugated linoleic acid rich vegetable oil production using heterogeneous catalysis

a technology of heterogeneous catalysis and vegetable oil, which is applied in the preparation of carboxylic compounds, fatty acid chemical modifications, organic chemistry, etc., can solve the problems of increasing the negative health risks of dietary animal fats, increasing the total fat and saturated fat intake, and increasing the alkaline catalytic process. achieve the effect of increasing the yield of cla

Inactive Publication Date: 2016-06-09
THE BOARD OF TRUSTEES OF THE UNIV OF ARKANSAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent is about a process for making a type of fat called CLA (conjugated linoleic acid) using different types of chemicals like organic proton donors, monosulfides, disulfides, mercaptans, or mixtures thereof. The process involves using formic acid, either alone or in combination with other chemicals, to increase the amount of CLA produced. Additionally, the process may also include using cysteine, a specific amino acid, to further enhance the amount of CLA produced.

Problems solved by technology

Obtaining the estimated optimum dietary CLA levels from natural beef and dairy sources would increase the total fat and saturated fat intake and increase the negative health risks associated with dietary animal fats.
The alkaline catalytic process, however, is unable to directly produce CLA-enriched vegetable oils because of competitive hydrolysis of triacylglycerol (TAG).
A drawback of these processes is the removal of the soluble catalyst from the CLA-rich oil before the product is suitable for human consumption.

Method used

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  • Conjugated linoleic acid rich vegetable oil production using heterogeneous catalysis
  • Conjugated linoleic acid rich vegetable oil production using heterogeneous catalysis
  • Conjugated linoleic acid rich vegetable oil production using heterogeneous catalysis

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0047]Example 1 demonstrates the unexpectedly superior results of formic acid mixed with soy oil, in the deodorizing steam supply and as a pretreatment of a transition metal catalyst on the CLA yield to reduce the need for a catalyst. In this Example, CLA-rich oil having up to 26% CLA in the oil was produced using 10% formic acid mixed with soy oil and 85% formic acid in the deodorizing steam when processed at 210° C. at <5 mm Hg pressure for 1-2 hours. Variable levels of 0-0.064% catalyst doses and processing time and temperatures were used to produce up to 26% CLA in the oil. Formic acid was recovered and reused from the condensate and the solid catalyst recovered from the oil. The CLA-rich vegetable oil was produced from RUBSO using a single step ruthenium-based heterogeneous catalysis method with a significantly reduced ruthenium catalyst dose.

[0048]RUBSO for Example 1 was obtained from Riceland Foods (Stuttgart, Ark.) with linoleic acid (55.9%) and linolenic acid (6.9%), as mea...

example 2

[0074]Example 2 demonstrates the production of CLA-rich vegetable oil with no or low trans-fat using a single step transition metal-based heterogeneous catalysis process with a catalyst promoted compound in the absence of hydrogen and air using an oil deodorizer to enhance the catalytic conversion rate from linoleic acid to CLAs in vegetable oils. In this Example 2, a synergistic augmentation effect of catalyst, formic acid and promoter on the production of CLA was determined, along with the effects of catalyst dose and the amount of promoter in the oil deodorizer on CLA yield.

[0075]Once refined, refined bleached deodorized soy oil (RBDSO) was obtained from Riceland Foods (Stuttgart, Ark.) with appropriate linoleic acid (55.9%) and linolenic acid (6.9%), as measured by GC-FID. Heptadecanoic acid methyl ester (17:0; Sigma-Aldrich, St. Louis, Mo.) was used as a standard for GC-FID analysis. Sodium methoxide and anhydrous sodium sulfate (EM Science, Darmstadt, Germany) were used for me...

example 3

[0087]Example 3 demonstrates the inventive process disclosed herein used to produce CLA-rich vegetable oil with no or low trans-fat using a single step transition metal-based, namely nickel, heterogeneous catalysis process with catalyst promoted compounds, namely organic acids and thiol compounds, in the absence of hydrogen and air with a hydrogenation unit to enhance the catalytic conversion rate from linoleic acid to CLAs in vegetable oils. In this Example 3, the synergistic augmentation effect of nickel catalyst, formic acid and cysteine on the production and yield of CLA was further demonstrated, along with effect of the operational parameters, namely temperature, processing time, mixing speed, and types of catalyst materials, on the CLA yield and the trans-oleic acid in the hydrogenation unit.

[0088]Similar to the other examples, once refined, RBDSO was obtained from Riceland Foods (Stuttgart, Ark.) with appropriate linoleic acid (55.9%) and linolenic acid (6.9%), as measured by...

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Abstract

The invention is directed to CLA-rich vegetable oil production from linoleic rich oils by heterogeneous catalysis. The process produces conjugated PUFA in triglyceride form, preferably at least 20% CLA-rich, by isomerization of a non-conjugated PUFA in vegetable oils using a heterogeneous transition metal catalyst promoted by an organic acid and / or thiol-containing compound. The heterogeneous catalysis isomerization process can use steam / vacuum distillation, hydrogenation unit and / or deodorization to produce CLA-rich soy oil. After processing, any catalyst residue may be removed by filtration, beaching, deodorizing, adsorbents or centrifugation to obtain high quality, CLA-rich oils.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of and priority to U.S. Provisional Patent Application Ser. No. 62 / 088,448, filed Dec. 5, 2014, which is incorporated herein by reference in its entirety.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT[0002]Not Applicable.NAMES OF THE PARTIES TO A JOINT RESEARCH AGREEMENT[0003]Not Applicable.REFERENCE TO A SEQUENCE LISTING, A TABLE, OR A COMPUTER PROGRAM LISTING APPENDIX[0004]Not Applicable.STATEMENT REGARDING PRIOR DISCLOSURES BY THE INVENTOR OR A JOINT INVENTOR[0005]Not Applicable.BACKGROUND OF THE INVENTION[0006]1. Field of the Invention[0007]This invention relates generally to conjugated linoleic acid (CLA)-rich oil production from linoleic rich vegetable oils by heterogeneous catalysis, and more particularly to a process for producing conjugated polyunsaturated fatty acids (PUFA) in triglyceride form, preferably CLA-rich oils, by isomerization of a non-conjugated PUFA in vegetable o...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C11C3/14
CPCC11C3/14
Inventor PROCTOR, ANDREWRUAN, CHUAN MIN
Owner THE BOARD OF TRUSTEES OF THE UNIV OF ARKANSAS